In 2011, Roosh wrote an article about the theories men have about the easiest days of the year to get laid. Valentine's Day was a common theory he heard about and wrote about in the article.
Valentine’s Day
Common Sense: Single girls feel especially lonely, so they’ll want to **** any guy that gives them a little attention.
The Reality: She’s fantasizing about love, not sex.
Most venues are going to be overrun by couples. If anything, I would say you are generally less likely to be successful with pickup on Valentine's Day than a normal, non-holiday. May actually be the only holiday you can actually say this is true.
And to be clear - not saying it can't happen depending on the venue.
I would agree that a lot of venues would be overrun by couples. However, a lot of venues that couples tend to go to are sit down restaurants, which aren't places that people go to meet women for same night lays or to arrange future dates.
I think that Valentine's Day in more pickup oriented nightlife venue would be fairly slow and maybe some couples who couldn't get a reservation at a romantic restaurant might be there.
One year, I went out to a bar that was good for pickup on Valentine's Day. I did some approaches, had a meaningful conversation, arranged a date, and collected a phone number. I think I got 2 dates out of that woman, no sex, and the interaction fizzled out.
Just wait for St Patrick's day. It's the seasonal time for banging. It falls on a Friday this year, too, so expect lots of partying.
This year, both St. Patrick's Day and Cinco de Mayo fall on Fridays. Cinco de Mayo is St. Patrick Day's with a Mexican theme.